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Single Life: The Best and Worst Dates

“You need to borrow $20? Are you kidding me?” was just one of many comments made on the worst date of my life.

This was back a few years when I was living on the coast of North Carolina. I had been talking with some friends, and they insisted that I go out with this guy they knew named Jason. I was like, "A blind date, seriously? Am I that desperate? Am I that lonely? Am I that crazy?” Well, I guess I was because I agreed.

I got a call from Jason to confirm our plans. He asked me if it was OK to pick me up a little earlier, say 4:30 p.m. I was like, “Sure, I mean I guess.” Hmmm, maybe he had something special planned for our first date. I could see it now: maybe a long horse ride on the beach, followed up with dinner on the sand while watching the sunset. Before I knew it, it was Saturday and 4:30 had fast approached. I waited a little anxiously to see who my best friends thought was a match for me. All of a sudden I heard this loud noise coming up the driveway. It was a large, beat-up, ugly truck, complete with black smoke spewing out of the tail pipe. I froze in mid-stare as I realized this was my date.

My first thought was which one of my friends would I kill first. This cannot be happening to me. Seriously, this is who they think I should be with? What did I do to them to deserve this? The truck finally stopped just short of my front door. I noticed that Jason decided to bring along his dogs for company.

As he got out of the truck, he yelled "You must be Krisssstyyyyy," drawing out my name like only a true redneck southern boy can do.

“No, I'm Kris,” I said, praying that maybe he had the wrong driveway. I tried to smile and be nice to him but clearly this had to be a joke. Maybe it was a set-up, and he really wasn't as country as he appeared. Maybe those weren't his dogs, and I was not about go to on this date. But unfortunately it was all true, and I just didn't have the heart to tell him my friends were playing a joke on us both. He asked if I was ready to go, and I was like, "As ready as I will ever be."

When I got into the truck, there was trash all over the seat—old Fritos bags, soda cans, and McDonald's wrappers. Jason quickly said he was sorry as he moved the trash to the floor board. The whole time I kept praying that I was in a bad dream. Jason said he had something special planned for us. He was taking me to one of his favorite restaurants for dinner. Based on what I was seeing now, I could only imagine where we were going.

“Hey, do you like Lynyrd Skynyrd ?”

“Uh, well, uh, well, not really.”

“Well, how ‘bout George Jones?”

“George who? OK, you must like ... um, it doesn't matter, Jason. Just play what you like. I am sure it will be just fine.” He pushed a few buttons and away we went, jamming out to Lynyrd.

As we started down the road, I noticed the windows were all down. I had started to roll up my window as it was pretty chilly outside, plus I had done my hair. I kept turning the handle, but it wasn't working. Jason said, “Oh, sorry, that window hasn't worked in years. If you're cold, you just need to slide closer to me. I can keep you warm.”

Did he just say that? I think I am going to gag. Well, I had no choice. I slid over, weaving my feet through the pile of food wrappers.

I said, “Well, can we at least close the window to the back of the truck. Or are they broken too? Your dogs keep licking my hair.”

“Aw, shucks, they're just saying hi. If they lick you, that means they like you.” I could feel the stomach juices turning over. Anytime I was about to add to the decor in his truck.

Well, to say the least I was still cold. Jason was not able to keep me completely warm. I said, "Jason, do you not have any heat in this truck?” He seemed frustrated with the question. He sighed heavily, and the next thing I knew he had his hands down near my calves.

I was startled and started to jump out the open window when Jason said, “I am not doing anything. The wires are all connected. If you want heat, I have to disconnect the radio to reconnect the heater.” At this point, I was ready to hitch home and take my chances with a serial killer picking me up.

I can see why God never mentions dating in the Bible. Dating can be hard. It's like “a box of chocolates,” to quote Forrest Gump. "You never know what you’re going to get." When I was a young adult, dating was like breathing. I dated continuously. It was easy to me. I mean, I wasn't dating to be married; I was dating to have fun. So when the occasional bad date occurred, I was like, “No problem. There will be another one around the corner.” But with age and maturity in Christ, I began to realize that God wants us to "date," or I say "court," with purpose. Otherwise it should be simply building friendships. I learned the dangers of dating to only meet my needs. I learned over time the value and meaning behind dating God's way. I learned to wait on God for his best, for his purpose—even if it meant being set up by friends. And even if it meant going through some really bad dates. And even some great ones.

I wait for the Lord, my soul waits, and in his word I put my hope (Psalms 130:5).

So the survey is out. What are some of your worse and best dates? Has God been teaching you anything as a result of them? See below for some of my friends’ fun and heart-filled answers.

CHERYL: Best Date

The best date was when I had some face-to-face time with an old friend (who I had once dated) for the last 25 years. He was in town for business. and we met at a local cafe. We shared the funniest and saddest moments in our lives as Christians—including the good, the bad and the ugly. We talked about our destiny and purpose. We shared how we can support each other in our ministries. We later went to pick strawberries. I then put him on a plane to return home. I couldn't image my life without his friendship. What a wonderful date.

Jonathan said to David, “Go in peace, for we have sworn friendship with each other in the name of the LORD, saying, ‘The LORD is witness between you and me, and between your descendants and my descendants forever.’” Then David left, and Jonathan went back to the town (1 Samuel 20:42).

DIANA: Worst Date

The guy was late. He talked about himself all during dinner. When the check came, he asked me to split it. He opened no doors, made little eye contact, was shallow and keep reminding me of what a good catch he was (he came highly recommended through a mutual acquaintance). Oh, he lost his key and asked me to drive him to get his spare, and he lived with his mom! I think even the Lord laughed at this evening.

It was Valentine’s. I had been dating this guy for a while. He knew I loved surprises. We decided to spend the day together. Every hour that went by, he let me put my hand in a big tote bag and pull out a new gift. Some of the gifts were simple like my favorite gum or soda, while others were bigger such as a CD or DVD. But all led up to an engagement ring. Yep, that was the best date ever.

A gift opens the way for the giver and ushers him into the presence of the great (Proverbs 18:16).

NEAL: Worst Date

I had a first date with this lady who I found interesting. I quickly decided I wanted a second date. But then it happened. She began to say,"It feels like I've known you my entire life. I feel like we can go the distance. I sense that we have a real connection. I believe I am falling in love with you." On the second date??? Needy much!? How well can a person know someone else at only the second time they see each other?

A fool’s mouth is his undoing, and his lips are a snare to his soul (Proverbs 18:7).

JENNY: Worst Date

This guy took me to Subway on our first date and paid for it with a gift card. Then we went back to his place, and he ended up putting in a horror movie. All that is pretty bad, but that's not what made it the worst date. What makes it my worst date is the choice I made that night. I was 30 and had never been kissed. He asked me if he could kiss me and I said he could. Unfortunately I made the choice to make out with this guy. STUPIDEST decision EVER. My first (and so far) only kisses were wasted on a man who really didn't want to get to know me. Some people may not think that is THAT bad, but for me that was the worst date ever.

Don’t let anyone look down on you because you are young, but set an example for the believers in speech, in life, in love, in faith and in purity (1 Timothy 4:12).

JEROME: Worst Date

I went to dinner with this very attractive lady (at least she had attractive Facebook pictures!). But when I met her in person, well ... it became apparent that she had had quite a few cosmetic "enhancements" in her lifetime. Overall, she seemed very athletic and fit ... but while observing her during dinner, I noticed her face was so pulled back so tight that she kept licking her lips every 3 to 4 seconds (reminded me of a lizard!) and stretching her lower jaw out. Talk about distracting! I don't remember much of the conversation. Heck, I can't even recall what I ordered for dinner.

Do you not know that your body is a temple of the Holy Spirit, who is in you, whom you have received from God? You are not your own (1 Corinthians 6:19).

TOM: Best Date

One of my favorite dates was when a good friend turned girlfriend e-mailed me some riddles on my birthday. Each riddle corresponded to a different location of our date. I had the best time trying to figure out what each meant. One location was where we would eat an appetizer, another one was our main meal, another an outdoor theatre production, and the last one was dessert and coffee and my birthday present. It was so much fun.

May those who delight in my vindication shout for joy and gladness; may they always say, “The LORD be exalted, who delights in the well-being of his servant” (Psalms 35:27).

KEISHA: Worst Date

This guy I've known for a few years (he cut my boy’s hair) came to me one day and said he wanted to talk to me. We went to the park and sat and talked for a while. Everything he said was as if God had told him what to say. He had goals and dreams. He really wanted to get to know me and see where it led. No rush—nice and slow. The next three days we texted each other, and it was great. We tried to set up a date, but he never got off in time. About a week later, he asked me for $150. I told him to meet me for dinner, and we would talk about it. I already knew the answer was no, but I wanted to actually sit and talk to him again. We had only been texting and occasionally talking on the phone. We had tried other nights, but he always had an issue or was working late. Finally I make it to the restaurant, and he was already sitting down eating. No, I was not late; he got there before me though. I came in and ordered a shake and sat down. He told me he needed the money to pay the cable guy to come wire the barber shop and to mount a flat screen television. He made all kinds of promises, said he would sign a promissory note and everything. I explained to him that I passed up a $14 pair of shoes that day because I didn't need them, and that my boys might need something. He said ok and he understood. He then got up and said 'I have to go catch up with my cousin to see if he got the money.' He left me there with my shake.

A greedy man stirs up dissension, but he who trusts in the LORD will prosper (Proverbs 28:25).

BOB: Worst Date

I had known this girl for a couple of years. I thought I knew her pretty well, so I asked her out. I took her to dinner for our first date. After a few minutes of chit chat, she asked me about Santa Claus. It was July. I was like, “What?” She wanted to know my view of Santa ... of whether I thought it was okay to celebrate Santa with kids. I explained it was okay to open gifts by way of St. Nicholas who was a real person who gave gifts secretly to poor children, as well as teaching about the celebration of giving gifts because of the Magi giving gifts to Christ. But I did not support lying to your kids about the mystical Santa. She then spent the next two hours telling how important it was for her to find someone who would tell kids about Santa Claus and the elves. I thought I was in The Twilight Zone.

The LORD detests lying lips, but he delights in men who are truthful (Proverbs 12:22).

BARBARA: Best Date

My best date was unexpected. My boyfriend and I were going on a night walk in the woods (with head lamps) which we often did. I didn't know that it was the night that the Northern Lights were visible (but he did). As always, he had his backpack and camera. He loved to take pictures everywhere we went. Anyway, he said, "This is a good spot." He open his backpack, took out the tripod, set up the camera, pulled out a blanket and we sat down. Well when the Northern Lights appeared, I was speechless. This was the best date ever ... so far that is.

He has made everything beautiful in its time. He has also set eternity in the hearts of men; yet they cannot fathom what God has done from beginning to end (Ecclesiastes 3:11).

DEBBIE: Worst Date

My ex-husband showed up on my date with my eventual new husband. Now that was awkward.

When pride comes, then comes disgrace, but with humility comes wisdom (Proverbs 11:2).

So, we finally arrived at Jason's favorite restaurant ... Golden Corral. I started to chuckle under my breath. We got there early to get the early bird special price. I thought, Wow, all this and cheap. How lucky can a girl get? As we walked in the door, you have to pay before you get your meal. Jason turned to me and asked me, "Hey, do you have $20 I can borrow?" Seriously dude? Seriously? I pulled a $20 out of my purse and paid for the meal. Sure, I could have told him to drop dead when he asked to borrow the money, but I didn't feel like walking home and I knew the cab ride would be more than $20. So at least this way I got to eat. After dinner Jason wanted to know if I wanted to go dancing. As I peeked in my wallet, I said, “No, can't afford it. Besides, your dogs will get awful lonely having to stay in the truck that long.” I asked Jason to take me home. At my front door he attempted to steal a kiss right after he spit some tobacco juice in a Coke bottle. I quickly turned my head and said, “Thanks, it was interesting.”

“Hey, I will call you and we can do it again.”

Yeah, sure, in heaven dude.

So what has all this taught me? To just seek the Lord in all things. As I draw closer to God, he will not only show me who I am suppose to date, but will also prepare the path of those dates. So whether your dates lead to marriage or not, just be intentional to put Christ first.

But seek first his kingdom and his righteousness, and all these things will be given to you as well (Matthew 6:33).

TheSinglesNetwork.org Ministries helps churches, pastors and single adult leaders evaluate, develop and support their single adult ministries through high-energy speaking engagements, results-oriented consulting and training and leadership development conferences and seminars. Click here to request a FREE "How to Start a Single Adult Ministry" guide.

FromHisHands.com Ministries is Kris' speaking ministry. If you've ever heard her speak, you know that Kris is the kind of speaker who keeps the crowd captivated, shares great information and motivates people to make a difference in the lives of those around them! She speaks to all church audiences on everything from "first impression" ministry to women's topics to singles and young adults. She can speak on a Sunday morning, at a woman's retreat or for a single adults conference. Bring Kris to your church today!